Ethylenediamine → 8-Bromo-3,4-dihydro-1H-benzo[e][1,4]diazepin-5(2H)-one

A mixture of 4-Bromo-2-fluoro-benzoic acid (500 mg, 2.28 mmol) and 5 mL Ethane-1,2-diamine was reacted in a sealed tube under argon with microwave irradiation at 150 C for 30 min. The reaction was cooled, diluted with methylene chloride (200 mL), and DMF (10 mL) to give a homogeneous solution. 2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU), (1 g, 2.63 mmol, 1.1 eq.) was added, and the reaction stirred at room temperature for 2 hours. The reaction was then heated to 95 C for 15 hours, cooled, and 3 mL 5 N NaOH was added. The mixture was stirred at room temperature for 1 hour, the reaction was concentrated in vacuo, extracted with ethyl acetate 3×, the organic layers were dried and concentrated. The residue was purified by flash chromatography to give 150 mg of 8-Bromo-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one, 27%.

1. customwas reacted in a sealed tube under argon with microwave irradiation at 150 C for 30 min
2. temperatureThe reaction was cooled
3. customto give a homogeneous solution
4. temperatureThe reaction was then heated to 95 C for 15 hours
5. temperaturecooled
6. stirringThe mixture was stirred at room temperature for 1 hour
7. concentrationthe reaction was concentrated in vacuo
8. extractionextracted with ethyl acetate 3×
9. customthe organic layers were dried
10. concentrationconcentrated
11. customThe residue was purified by flash chromatography

ORD 기록

ord-36cb8ebecd1e4602bed9b23e1eb49317

출처 데이터셋

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08318719B2